OCTANE-BOOSTING FUEL ADDITIVES, METHOD OF MANUFACTURE, AND USES THEREOF

• US 20200131448A1
• Filed: 03/19/2018
• Published: 04/30/2020
• Est. Priority Date: 03/22/2017
• Status: Active Grant

• Current Assignee: SABIC Global Technologies BV (Government of Saudi Arabia)
• Original Assignee: SABIC Global Technologies BV (Government of Saudi Arabia)
• Inventors: BODAS, Vijay Dinkar, AL-OTAIBI, Sultan Eid, LEAL, Guillermo, ANSARI, Mohammed Bismillah, AL-OTAIBI, Naif Mohammed Al Naddah
• Granted Patent: US 11,008,525 B2
• Time in Patent Office: Days
• CPC Class Codes: C10L 1/023 for spark ignition
• CPC Class Codes: C10L 1/1817 Compounds of uncertain formula; reaction products where mixtures of compounds are obtained
• CPC Class Codes: C10L 1/1855 Cyclic ethers, e.g. epoxides, lactides, lactones
• CPC Class Codes: C10L 10/10 for improving the octane number
• CPC Class Codes: C10L 2200/0423 Gasoline
• CPC Class Codes: C10L 2270/023 for gasoline engines

Abstract

A method of manufacturing an octane-boosting fuel additive, the method comprises reacting n-butyraldehyde, iso-butyraldehyde, or a combination comprising at least one of the foregoing with glycerol in the presence of an acidic catalyst to obtain an octane-boosting product mixture comprising 2-propyl-5-hydroxy-1,3-dioxane, 2-isopropyl-5-hydroxy-1,3-dioxane, 2-propyl-5-hydroxymethyl-1,3-dioxolane, 2-isopropyl-5-hydroxymethyl-1,3-dioxolane, or a combination comprising at least one of the foregoing.

Claims

1. A method of manufacturing an octane-boosting fuel additive, the method comprising

reacting n-butyraldehyde, iso-butyraldehyde, or a combination comprising at least one of the foregoing with glycerol in the presence of an acidic catalyst to obtain an octane-boosting product mixture comprising 2-propyl-5-hydroxy-1,3-dioxane, 2-isopropyl-5-hydroxy-1,3-dioxane, 2-propyl-5-hydroxymethyl-1,3-dioxolane, 2-isopropyl-5-hydroxymethyl-1,3-dioxolane, or a combination comprising at least one of the foregoing.

2. The method of claim 1, wherein the n-butyraldehyde, iso-butyraldehyde, or combination comprising at least one of the foregoing is a by-product of butanol or 2-ethylhexanol production.

3. The method of claim 2, wherein the by-product is a crude by-product.

4. The method of claim 3, wherein the crude by-product is undistilled.

15. The method of claim 4, wherein the acidic catalyst comprises p-toluene sulphonic acid, zinc stearate, tetraisopropyl titanate, or a combination comprising at least one of the foregoing;

wherein the acidic catalyst is present in an amount of 0.05 to 5 weight percent, based on the total weight of the aldehyde and the glycerol;

wherein the reacting is performed at 0.5 to 5 bar and a temperature of 0°

C. to 175°

C.; and

further comprising removing the acidic catalyst from the product mixture.

16. An octane-boosting fuel additive made by the method of claim 1.

17. An unleaded gasoline composition comprisingto 99.8 volume percent of an unleaded gasoline;

and

0.2 to 20 volume percent of the octane-boosting fuel additive of claim 16;

wherein the unleaded gasoline composition has a higher Research Octane Number, determined in accordance with ASTM D 2699, and a higher Motor Octane Number, determined in accordance with ASTM D 2700, than the unleaded gasoline without the octane-boosting fuel additive.

18. The unleaded gasoline composition of claim 17, having a Reid Vapor Pressure lower than the unleaded gasoline without the octane-boosting fuel additive, wherein Reid Vapor Pressure is determined in accordance with ASTM D 323.

5. A method of manufacturing an octane-boosting fuel additive, the method comprising

reacting 2-ethylhexenaldehyde, 2-ethylhexaldehyde, or a combination comprising at least one of the foregoing with glycerol in the presence of an acidic catalyst to obtain an octane-boosting product mixture comprising 2-(hept-3-en-3-yl)-5-hydroxy-1,3-dioxane, 2-(heptan-3-yl)-5-hydroxy-1,3-dioxane, 2-(hept-3-en-3-yl)-5-hydroxymethyl-1,3-dioxolane, 2-(heptan-3-yl)-5-hydroxymethyl-1,3-dioxolane, or a combination comprising at least one of the foregoing.

6. The method of claim 5, wherein the 2-ethylhexenaldehyde, 2-ethylhexaldehyde, or a combination comprising at least one of the foregoing is a by-product of butanol or 2-ethylhexanol production.

7. The method of claim 6, wherein the by-product is a crude by-product.

8. The method of claim 5, wherein the acidic catalyst comprises p-toluene sulphonic acid, zinc stearate, tetraisopropyl titanate, or a combination comprising of at least one of the foregoing.

9. The method of claim 5, wherein the acidic catalyst is present in an amount of 0.05 to 5 weight percent, based on the total weight of the aldehyde and the glycerol.

10. The method of claim 5, wherein the reacting is performed at 0.5 to 5 bar and a temperature of 0°

C. to 175°

C.

11. The method of claim 5, further comprising removing the acidic catalyst from the product mixture.

12. An octane-boosting fuel additive made by the method of claim 5.

13. An unleaded gasoline composition comprisingto 99.8 volume percent of an unleaded gasoline;

and

0.2 to 20 volume percent of the octane-boosting fuel additive of claim 12;

wherein the unleaded gasoline composition has a higher Research Octane Number, determined in accordance with ASTM D 2699, and a higher Motor Octane Number, determined in accordance with ASTM D 2700, than the unleaded gasoline without the octane-boosting fuel additive.

14. The unleaded gasoline composition of claim 13, having a Reid Vapor Pressure lower than the unleaded gasoline without the octane-boosting fuel additive, wherein Reid Vapor Pressure is determined in accordance with ASTM D 323.

19. The method of claim 7, wherein the acidic catalyst comprises p-toluene sulphonic acid, zinc stearate, tetraisopropyl titanate, or a combination comprising at least one of the foregoing;

wherein the acidic catalyst is present in an amount of 0.05 to 5 weight percent, based on the total weight of the aldehyde and the glycerol;

wherein the reacting is performed at 0.5 to 5 bar and a temperature of 0°

C. to 175°

C.; and

further comprising removing the acidic catalyst from the product mixture.